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Thionyl chloride

Manufactured by Thermo Fisher Scientific
Sourced in Belgium, United States

Thionyl chloride (SOCl2) is a colorless, fuming liquid chemical compound. It is a common reagent used in organic synthesis, typically as a chlorinating agent or for the preparation of acid chlorides. Thionyl chloride has a pungent odor and is highly reactive with water.

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16 protocols using thionyl chloride

1

Synthesis and Characterization of Ibuprofen Derivatives

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All used in this research reagents were commercially available materials and were used without further purification. (R,S)-Ibuprofen (>98%) was provided from Am-Beed (Arlington Heights, IL, USA). Thionyl chloride (99.5%) was obtained from Acros Organics (Geel, Belgium). l-Histidine (≥99%) and l-phenylalanine (>98.5%) were purchased from Carl Roth (Karlsruhe, Germany). l-Tyrosine, acetonitrile (≥99.9%) for HPLC gradient grade, deuterated DMSO (99.9%), 2-ethylhexyl acrylate (2-EHA) (98%), isobornyl methacrylate (IBOMA) (>99%), azobis(isobutyronitrile) (AIBN) (99%), and n-octanol (≥99%) were provided by Sigma-Aldrich (Steinheim am Albuch, Germany). l-Tryptophan was provided by Tokyo Chemical Industry Co., Ltd (TCI, Tokyo, Japan). Propanol (PrOH), ammonium hydroxide solution 25% (NH3·H2O), anhydrous sodium sulfate, n-hexane, methylene chloride, and diethyl ether were high-purity obtained from Chempur (Gliwice, Poland). 4-Acryloyloxy benzophenone (ABP) was obtained from POLY-CHEM BmbH (Bitterfeld-Wolfen, Germany). Acrylic acid (AA) (>98%), ethanol (EtOH), chloroform, toluene, and ethyl acetate were of analytical grade purchased from StanLab (Lublin, Poland). Deuterated chloroform (CDCl3) (99.8%) (+0.03% TMSCl) was purchased from Eurisotop (Cheshire, England).
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2

Cytotoxicity Evaluation of Carbon Nanotubes

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The 3-(4,5-dimethylthialzol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and L-glutamine were acquired from Sigma Company (St. Louis, MO, USA). Nitric and sulfuric acid,
tetrahydrofuran, and thionyl chloride were purchased from Acros Organics (Morris Plains, NJ, USA) and fetal bovine serum (FBS) and RPMI 1640 from Biosera (Nuaillé, France).
Streptomycin-penicillin and the Jurkat cell line were obtained from Gibco (Gaithersburg, MD, USA) and the National Center for Genetic and Biological Resources of Iran (Tehran, Iran),
respectively. Crude SWCNTs and MWCNTs were made at the Petroleum Industry Research Institute (RIPI, Tehran, Iran). The HPLC reagents and solvents or those of analytical grade
used in this study were procured from Merck Millipore (Burlington, MA, USA). The kit of RNA extraction was from Bio Basic Inc. (Markham, Canada) and the kits of cDNA synthesis
and SYBR Green Master Mix from Takara Bio Inc. (Kyoto, Japan).
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3

Synthesis and Purification of PCL-b-PEG

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The following analytical-grade chemicals were purchased and used without further purification: 2,3,5-triiodobenzoic acid (Changzhou Ilhang Fine Chemical Co. Ltd, China), thionyl chloride (Acros Organics, 99.5%), sodium carbonate, dichloromethane (Acros Organics, 99.9%). N-methyl-2pyrrolidone (NMP, 99.5%), pyridine (99.5%) and 4dimethylaminopyridine (DMAP, 99.5%) were purchased from Acros Organics in anhydrous grade over molecular sieves in an AcroSeal packaging. Poly(vinyl alcohol) (PVAL, Sigma-Aldrich, 98% hydrolyzed, average molar mass MW = 13,000-23,000 Da) was dried at 40 °C in an oven for 24 h under vacuum before use. Tetrahydrofuran (THF, Fisher Scientific), absolute anhydrous ethanol (Carlo Erba) were used in purification processes. The polycaprolactone-block-poly(ethylene glycol) (PCL-b-PEG block copolymer) was synthesized by polymerization of caprolactone initiated by poly(ethylene glycol) monomethyl ether catalyzed by tin octanoate as reported in refs 58, 59 The degrees of polymerization of the poly(caprolactone) and. poly(ethylene glycol) blocks were 65 and 113 respectively (PCL65-b-PEG113). Deionized water of 18 Ω•cm resistivity was used for all preparations.
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4

Palladium-Catalyzed Benzoquinone Synthesis

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All reagents
were of analytical grade and used without further purification. Citric
acid and thionyl chloride were supplied by Thermo Fisher Scientific.
Palladium chloride, BDA, and BTC (99%) were supplied by TCI. Methanol
(MeOH) and 1,4-benzoquinone were supplied by Sigma-Aldrich. Dimethylformamide
(DMF) and diethyl ether were supplied by Spectrochem. Triethylamine,
ethanol (EtOH), isopropanol, and EDTA were procured from SDFCL, Spectrum,
Merck, and SRL, respectively. THF was dried over the sodium metal
and benzophenone under an inert atmosphere.
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5

Extraction and Analysis of Bioactive Compounds

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Technical-grade methanol, n-hexane, chloroform, dichloromethane and isobutanol, HPLC grade water, formic acid, acetonitrile, and methanol were provided by CHEM-LAB NV (Somme-Leuze, Belgium). 2,5-dihydroxybenzoic acid (DHB), N,N-dimethylaniline (DMA), Hederacoside C and potassium methanolate were purchased from Sigma-Aldrich (Diegem, Belgium). Phosphoric acid, borax, sodium hydroxide and hydrochloric acid were provided by VWR Chemicals (Leuven, Belgium), while thionyl chloride, p-toluenesulfonic acid, sulfuric acid and DowexTM resin were purchased from Thermo Scientific (Merelbeke, Belgium).
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6

Synthesis and Characterization of Multifunctional Nanoparticles

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Tetraethyl orthosilicate (TEOS), 1H-imidazole-4-carboxylic acid, thionyl chloride (SOCl2), Traut’s reagent (2-iminothiolane), Triton X-100, acetone, ethanol, glutathione (GSH), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), N-hydroxysuccinimide (NHS), tris(2-carboxyethyl)phosphine hydrochloride (TCEP) and ammonia (30% in water) were purchased from Fisher Scientific, USA. Hexanol, cyclohexane, and (3-aminopropyl)triethoxysilane (APTES) were bought from Tokyo Chemical Industry Co., Ltd., USA. Triethylamine (TEA) and dimethyl sulfoxide (DMSO) were purchased from Alfa Aesar, USA. Bis[3-(triethoxysilyl)propyl]-disulfide (BTPD) was purchased from Gelest, Inc., USA. Methoxy-poly(ethylene glycol)-silane (mPEG-silane, Mn = 5000), amine-poly(ethylene glycol)-silane (NH2-PEG-silane, Mn = 5000) and maleimide-poly(ethylene glycol)-silane (Mal-PEG-silane, Mn = 5000) were purchased from Biochempeg Scientific Inc., USA. All-trans-retinoic acid (ATRA) and 4-aminophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside were purchased from Santa Cruz Biotechnology, USA. Nuclear localization signal (NLS)-tagged Streptococcus pyogenes Cas9 nuclease (sNLS-SpCas9-sNLS) was obtained from Aldevron, USA. In vitro transcribed single guide RNAs (sgRNAs) and ssODNs were purchased from Integrated DNA Technologies, Inc., USA.
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7

Fullerene Functionalization Protocol

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All chemicals used were of reagent-grade quality or better. Solvents were dried in accordance with standard literature procedures. The following reagents were used as received: C60 (99.5+%, SES Research, USA), glycine tert-butyl hydrochloride (Sigma Aldrich, USA), malonic acid (Sigma Aldrich, USA), DBU (1,8-diazabicyclo[5.4.0]undec-7-ene, Sigma Aldrich, USA), triethylamine (Fisher, Belgium), CBr4 (Sigma Aldrich, USA), 1,4-dioxane (Acros Organics, Belgium), thionyl chloride (Fisher, UK), dichloromethane (Chempur, Poland), anhydrous sodium sulfate (POCH, Poland), diethyl ether (Eurochem, Poland), ethyl acetate (POCH, Poland), toluene (Chempur, Poland), methanol (Chempur), and concentrated hydrogen chloride (POCH, Poland).
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8

Synthesis and Characterization of EPR-Labeled EOC

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4-Hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl (HO-T) (Fisher Scientific Italia, Milan, Italy), 4-benzoyloxy-2,2,6,6-tetramethyl-piperidine-1-oxyl (Bz-T) (Fisher Scientific Italia), 3,5-di-tert-butyl-4-hydroxybenzoic acid (Fisher Scientific Italia), thionyl chloride (Fisher Scientific Italia), triethylamine (Fisher Scientific Italia), di(tert-butylperoxy-isopropyl) benzene (mixture of isomers) (P14) (Perkadox 14S-FL, Akzo Nobel, Amsterdam, The Netherlands) and 3,5-di-tert-butyl-4-hydroxybenzoic acid hexadecyl ester (CY, Cyasorb 2908 kindly supplied by Prof. Cristian Gambarotti, University of Milano, Milan, Italy) were used as received. A random copolymer ethylene/α-olefin (EOC) having density = 0.9 g/cm3 and Mn ≈ 90,000 D was used as polymer matrix. EOC has melting point between 50 and 70 °C [39 (link)] and Tonset about 430 °C (TGA analysis carried out under nitrogen) [25 (link)]. Pre-coated aluminum F254 silica gel 60 sheets were used for TLC analyses. Purification by chromatography was performed using silica gel Merck 60 (particle size 0.040–0.063 mm) (Merck KGaA, Darmstadt, Germany). All reactions were performed under nitrogen. The sample EOC-g-(Bz-T) where 4-benzoyloxy-2,2,6,6-tetramethyl-piperidine-1-oxyl (Bz-T) is grafted to EOC was prepared as previously reported [22 (link)].
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9

Synthesis of Organic Compounds and Peptides

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2,2,6,6-Tetramethyl-1-piperidinyloxy (TEMPO), substance P (RPKPQQFFGLM), 4,4`-dinonyl-2,2`-dipyridyl, N-hydroxy-succinimide, methyl(4-bromomethyl) benzoate were purchased from Sigma Aldrich (St. Louis, MO). Water, MS-grade methanol, acetonitrile, 2-(bromomethyl)benzoic acid, toluene, dicholormethane, tetrahydrofuran, copper (II) trifluoro-methanesulfonate, thionyl chloride, N, N-dicyclohexylcarbodiimide, triethylamine (TEA), and formic acid were acquired from Fisher Scientific (Waltham, MA). ACTH (1–14) (SYSMEHFRWGKPVG), angiotensin I (DRVYIHPFHL), melittin (GIGAVLKVLTTGLPALISWIKRKRQQ-NH2), and amyloid β-peptide (10–20) (YEVHHQKLVFF) were purchased from Bachem (Bubendorf, Switzerland).
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10

Synthesis and Characterization of Biomolecular Compounds

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2,2,6,6-Tetramethyl-1-piperidinyloxy (TEMPO), substance P (RPKPQQFFGLM), 4,4`-dinonyl-2,2`-dipyridyl, N-hydroxy-succinimide, methyl(4-bromomethyl) benzoate were purchased from Sigma Aldrich (St. Louis, MO). Water, MS-grade methanol, acetonitrile, 2-(bromomethyl)benzoic acid, toluene, dicholormethane, tetrahydrofuran, copper (II) trifluoro-methanesulfonate, thionyl chloride, N, N-dicyclohexylcarbodiimide, triethylamine (TEA), and formic acid were acquired from Fisher Scientific (Waltham, MA). ACTH (1-14) (SYSMEHFRWGKPVG), angiotensin I (DRVYIHPFHL), melittin (GIGAVLKVLTTGLPALISWIKRKRQQ-NH 2 ), and amyloid β-peptide (10-20) (YEVHHQKLVFF) were purchased from Bachem (Bubendorf, Switzerland).
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